Determination of Absolute Configurations of Tertiary Alcohols by NMR Spectroscopy

A method has been developed for determining the absolute configurations of acyclic tertiary alcohols using their 2NMA [methoxy-(2-naphthyl)acetic acid] esters. The 1H NMR spectra of (R)- and (S)-2NMA esters of model compounds were measured, and (delta)(delta) values ((delta)R-ester - (delta)S-ester) were calculated. The absolute configuration for tertiary hydroxy group is determined based on the sign of (delta)(delta) values like that for secondary hydroxy group.